Citation: Zhang Chenglu, Wang Huayu, Yu Xiangkun, Yang Jingyi, Li Chuanyin, Gong Rongqin, Song Fulu, Sun Yuedong. Synthesis of Amide Thioether Bridged 1, 3-Selenazole and 1, 2, 4-Triazole Derivatives and Their Inhibitory Activity against Cell Division Cycle Phosphatase B (Cdc25B)[J]. Chinese Journal of Organic Chemistry, ;2020, 40(2): 432-439. doi: 10.6023/cjoc201907020 shu

Synthesis of Amide Thioether Bridged 1, 3-Selenazole and 1, 2, 4-Triazole Derivatives and Their Inhibitory Activity against Cell Division Cycle Phosphatase B (Cdc25B)

School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029

Corresponding author: Zhang Chenglu, zhangchenglu@lnnu.edu.cn
Received Date: 14 July 2019
Revised Date: 27 September 2019
Available Online: 12 February 2019
Fund Project: Project supported by the Science and Technology Research Program of Liaoning Provincial Department of Education (No. 2009A426)the Science and Technology Research Program of Liaoning Provincial Department of Education 2009A426

Figures(3)

The cell division cycle 25 phosphatase B (Cdc25B) is involved in carcinogenic transformation and is a potential drug target for anticancer therapy. In order to screen Cdc25B inhibitors, 1, 3-selenazole was selected as the core block, and 1, 2, 4-triazole Schiff base was bridged into 2-(1, 2, 4-triazol-3-yl)thio-N-(4-phenyl-1, 3-selenazolyl-2-yl)acetamide (TATS) by the amide thioether bond. The molecular docking simulation of TATS1 with Cdc25B was first performed to identify the rationality of the core function of 1, 3-selenazole. The results show that 1, 3-selenazole can be tightly embedded in the Cdc25B structure and perform N-H…PI non-bond weak interaction with the important catalytic site Arg492, which indicates that 1, 3-selenazole plays a central role. The amide carbonyl oxygen atom forms a hydrogen bond with Arg492 and Arg488, indicating that the introduction of the amide thioether bond is reasonable. Based on the theoretical docking study, thirteen new target compounds TATS1~TATS13 were designed and synthesized through modification in two regions of 1, 2, 4-triazole Schiff base. The inhibition against Cdc25B of target molecules and important intermediates was tested respectively. As a result, the inhibitory activities of the intermediates are not good, 12 target compounds have better biological activity than the positive reference substance Na₃VO₄, the modifications of two regions of 1, 2, 4-triazole also have a significant effect, which suggests that these compounds are expected to be a potential inhibitor of Cdc25B.
- 1, 3-selenazole,
- 1, 2, 4-triazole Schiff base,
- molecular docking simulation,
- Cdc25B inhibitor
1. [1]
  Park, H.; Bahn, Y. J.; Jung, S. K.; Jeong, D. G.; Lee, S. H.; Seo, I.; Yoon, T. S.; Kim, S. J.; Ryu, S. E. Eur. J. Med. Chem. 2008, 51, 5533. doi: 10.1021/jm701157g
2. [2]
  Song, W. Z.; Zheng, N. Org. Lett. 2017, 19, 6200. doi: 10.1021/acs.orglett.7b03123
3. [3]
  Song, W. Z.; Zheng, N.; Li, M.; Dong, K.; Li, J. H.; Ullah, K.; Zheng, Y. B. Org. Lett. 2018, 20, 6705. doi: 10.1021/acs.orglett.8b02794
4. [4]
  Pirrung, M. C.; Blume, F. J. Org. Chem. 1999, 64, 3642. doi: 10.1021/jo982503h
5. [5]
  Baston, E.; Palusczak, A.; Hartmann, R. W. Eur. J. Med. Chem. 2000, 35, 931. doi: 10.1016/S0223-5234(00)01167-3
6. [6]
  Chimenti, F.; Bizzarri, B.; Bolasco, A.; Secci, D.; Chimenti, P.; Granese, A.; Carradori, S.; Ascenzio, M. D.; Lilli, D.; Rivanera, D. Eur. J. Med. Chem. 2011, 46, 378. doi: 10.1016/j.ejmech.2010.10.027
7. [7]
  Bondock, S.; Naser, T.; Ammar, Y. A. Eur. J. Med. Chem. 2013, 62, 270. doi: 10.1016/j.ejmech.2012.12.050
8. [8]
  Makam, P.; Kankanala, R.; Prakash, A.; Kannan, T. Eur. J. Med. Chem. 2013, 69, 564. doi: 10.1016/j.ejmech.2013.08.054
9. [9]
  Yuan, J. W.; Wang, S. F.; Luo, Z. L.; Qiu, H. Y.; Wang, P. F.; Zhang, X.; Yang, Y. A.; Yin, Y.; Zhang, F.; Zhu, H. L. Bioorg. Med. Chem. Lett. 2014, 24, 2324. doi: 10.1016/j.bmcl.2014.03.072
10. [10]
  Chandrappa, S.; Chandru, H.; Sharada, A. C.; Vinaya, K.; Ananda, Kumar, C. S.; Thimmegowda, N. R.; Nagegowda, P.; Karuna Kumar, M.; Rangappa, K. S. Med. Chem. Res. 2010, 19, 236. doi: 10.1007/s00044-009-9187-7
11. [11]
  Lu, Y.; Li, C. M.; Wang, Z.; Ross, C. R.; Chen, J.; Dalton, J. T.; Li, W.; Miller, D. D. J. Org. Chem. 2009, 52, 1701.
12. [12]
  Romagnoli, R.; Baraldi, P. G.; Carrion, M. D.; Lopez, O. C.; Cara, C. L.; Basso, G.; Viola, G.; Khedr, M.; Balzarini, J.; Mahboobi, S.; Sellmer, A.; Brancale, A. J. Org. Chem. 2009, 52, 5551.
13. [13]
  Franchetti, P, ; Cappellacci, L.; Sheikha, G. A.; Jayaram, H. N.; Gurudutt, V. V.; Sint, T.; Schneider, B. P.; Jones, W. D.; Goldstein, B. M.; Perra, G.; Montis, A. J. Cheminformatics 2010, 25, 1731.
14. [14]
  Zhao, G. L.; Shi, X.; Zhang, J. P.; Liu, J. F.; Xian, H. D.; Shao, L. X. Sci. China:Chem. 2010, 40, 1525(in Chinese).
15. [15]
  Guan, Q. Y.; Xia, S.; Shen, J. B.; Zhao, G. L. Sci. China:Chem. 2013, 56, 588.
16. [16]
  Rohr W.; Staab, H. A. Angew. Chem., Int. Ed. 1965, 4, 1073. doi: 10.1002/anie.196510731
17. [17]
  Xie, W.; Zhang, J.; Ma, X.; Yang, W. Q.; Zhou, Y.; Tang, X. F.; Zou, Y.; Li, H.; He, J. J.; Xie, S. M.; Zhao, Y. H.; Liu, F. P. Chem. Biol. Drug Des. 2015, 86, 1087. doi: 10.1111/cbdd.12577
18. [18]
  Yang, B.; He, Q. J.; Zhu, D. Y.; Lou, Y. J.; Fang, R. Y. Cancer Chemother. Pharmacol. 2006, 57, 268. doi: 10.1007/s00280-005-0049-9
19. [19]
  Xia, L.; Fan, Z. J.; Yao, J. H.; Li, W.; Qua, F. Q.; Peng, L. Bioorg. Med. Chem. Lett. 2006, 16, 2693. doi: 10.1016/j.bmcl.2006.02.023
20. [20]
  Aiken, S. P.; Brown, W. M. Front. Biosci. 2000, 5, 124.
21. [21]
  Bekircan, O.; Bektas, H. Molecules 2006, 11, 469. doi: 10.3390/11060469
22. [22]
  Ghosh, S.; Tiwari, P.; Pandey, S.; Misra, A. K.; Chaturvedi, V.; Gaikwad, A.; Bhatnagar, S.; Sinha, S. Bioorg. Med. Chem. Lett. 2008, 18, 4002. doi: 10.1016/j.bmcl.2008.06.004
23. [23]
  Ozkay, Y.; Işikdağ, I.; Incesu, Z.; Akalın, G. Eur. J. Med. Chem. 2010, 45, 3320. doi: 10.1016/j.ejmech.2010.04.015
24. [24]
  Zhang, C. L.; Sun, X. N.; Pu, Y. X.; Li, C. Y.; Sun, L. J.; Wang, J.; Li, Y. Z. Chin. J. Org. Chem. 2017, 37, 440(in Chinese).
25. [25]
  Panda, S.; Nayak, S. Supramol. Chem. 2015, 27, 679. doi: 10.1080/10610278.2015.1075533
26. [26]
  Zhang, C. L.; Tang, J.; Yin, L. Y.; Xi, H.; Guo, Y.; Sun, L. J. Chin. J. Org. Chem. 2016, 36, 358(in Chinese).
27. [27]
  Liu, B.; Xu, C. D.; Zhou, X. J. Chem. Reag. 1993, 15, 334.
28. [28]
  Wolf, L.; Quoos, N.; Mayer, J. C. P.; Souza, D. D.; Sauer, A. C.; Meichtry, L.; Bortolotto, V.; Prigol, M.; Rodrigues Oscar, E. D.; Dornelles, L. Tetrahedron Lett. 2016, 57, 1031. doi: 10.1016/j.tetlet.2016.01.079
29. [29]
  Rakse, M.; Karthikeyan, C.; Deora, G. S.; Moorthy, N. S. H. N.; Rathore, V.; Rawat, A. K.; Srivastava, A. K.; Trivedi, P. Eur. J. Med. Chem. 2013, 70, 469. doi: 10.1016/j.ejmech.2013.10.030
1. [1]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
2. [2]
  Yihui Song , Shangshang Qin , Kai Wu , Chengyun Jin , Bin Yu . 生物化学在高水平创新型药学人才培养中的交叉融合应用——以去甲基化酶LSD1抑制剂的活性评价为例. University Chemistry, 2025, 40(6): 341-352. doi: 10.12461/PKU.DXHX202406018
3. [3]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
4. [4]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
5. [5]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
6. [6]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
7. [7]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
8. [8]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
9. [9]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
10. [10]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
11. [11]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
12. [12]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
13. [13]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
14. [14]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
15. [15]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
16. [16]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
17. [17]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
18. [18]
  Yanyang Li , Zongpei Zhang , Kai Li , Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020
19. [19]
  Yaping Li , Sai An , Aiqing Cao , Shilong Li , Ming Lei . The Application of Molecular Simulation Software in Structural Chemistry Education: First-Principles Calculation of NiFe Layered Double Hydroxide. University Chemistry, 2025, 40(3): 160-170. doi: 10.12461/PKU.DXHX202405185
20. [20]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(2100)
HTML views(189)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142